


Stuck in the Middle With You

by orphan_account



Category: IT (1990), IT (2017)
Genre: 1990 Pennywise, 2017 Pennywise, Bad Parenting, Blow Jobs, Cunnilingus, Daddy Kink, Daddywise, Dirty Talk, Dom/sub, Domestic Fluff, F/M, Fluff and Smut, Heavy Petting, Humiliation, Implied/Referenced Domestic Violence, Mildly Dubious Consent, Multi, Oral Sex, POV Female Character, Pennywise is his own Warning, Pet Names, Possessive Behavior, Power Dynamics, Power Play, Rough Oral Sex, Sequel to My Funny Valentine, Smut, Threats of Rape/Non-Con, Threats of Violence, Threesome - F/M/M, Unhealthy Relationships, Vaginal Fingering, Verbal Humiliation, Voyeurism, Weird Plot Shit
Language: English
Status: Completed
Published: 2017-10-17
Updated: 2017-10-16
Packaged: 2019-01-18 11:23:03
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 3
Words: 4,137
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12387084
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: So, 1990!Penny is still your Daddy, but it’s slightly more complicated now, with his offspring on the scene. 2017!Penny keeps turning up, wanting a repeat of your Valentine’s Day antics, and your Penny isn’t great at sharing, tbh.Still, it’s a lot of fun, when they’re not at each other’s throats.Sequel to 'My Funny Valentine.'





	1. Chapter 1

**Author's Note:**

  * For [Mualhani](https://archiveofourown.org/users/Mualhani/gifts), [Beastlybfs](https://archiveofourown.org/users/Beastlybfs/gifts), [DJSpidersGeorg](https://archiveofourown.org/users/DJSpidersGeorg/gifts).



> Yeah, I’m back again, with more clown smut.  
> No regrets. I have found my people, down here in the Derry sewer system, and I am loving it.
> 
> So, plot summary. Yeah, ha-ha, what plot?  
> Nah, there is one. Mostly smut, but there’s other stuff. 
> 
> Got loads more plans for future stories, when I’m not so busy, so thought I’d put some of my ideas out there, see what you guys think. 
> 
> 1\. A sequel to this fic. The finale! Following the novel (and film) canon, the Losers will arrive in Derry as adults, to take down Daddy Penny and Mini Penny. Reader will get caught up in the ensuing chaos. There’ll be sex, obviously, and a lot of angst.  
> 2\. AU, in which Daddy Penny and Mini Penny are human. I’m thinking 1950s, they are actual clowns in a family-run circus, and Reader marries into the dysfunctional clan. 1990s Penny as her sugar daddy husband and 2017 Penny as his bat-shit son, who also takes a fancy to Reader. More sex, more chaos.  
> 3\. Slight AU, in which Reader falls pregnant as a result of her hijinks with alien clown dicks, against the odds. No way of telling who the father is, so both clowns decide to put their differences aside and take an active role in the pregnancy/labour/parenting of Reader’s child. Weird hybrid baby and protective daddy clowns. Pregnant sex.  
> 4\. Vague sequel to this fic. No real plot, just lots of sex and character study. Reader trying to keep both clowns happy. Exploring the changing relationship/dynamics between the trio - focus on how different the clowns are, in their approach to Reader and their sexual preferences. Threesomes aplenty. Daddy Penny trying to keep Mini Penny from eating Reader. 
> 
> Let me know what you think, in the comments, along with your feedback/criticisms/whatever. And feel free to contribute more ideas - I love writing for this fandom!

It’s a blustery afternoon in March when you start to realise that maybe Valentine’s Day had been a mistake. Perhaps not entirely, but Pennywise’s gift had probably been ill-advised. Uncharacteristically reckless, to say the least.

You arrive home from grocery shopping, laden down with bags, and kick off your shoes in the hallway…only to step in something _wet_. You wince, setting your groceries down; your socks are soaked.

“Ugh, what the fuck…”

Hopping from foot to the other, you peel off your socks, tossing them aside. At first, you wonder if Frank has had a little accident, but the cat is smart and he always goes outside to do his business, through the cat-flap and into the backyard. Still, he’s just a cat, and he has been more stressed than usual. You study the wet patch closely and notice that there are more wet patches, a trail leading to the kitchen. Sniffing, you eliminate Frank from the line-up; whatever it is, it certainly doesn’t smell like cat piss.

It smells sweet and vaguely familiar.

_Where do I know that smell from?_

Sighing, you head into the kitchen with your groceries, skirting around the wet lines upon the floor and making a mental note to clean it up, once you’ve finished in the kitchen.

_But first, caffeine._

The kitchen is dark, despite the large windows. Outside, the sun is weak, veiled in grey cloud. You turn on the light and place the bags upon the table, shrugging out of your coat.

“Frank? Frank, I’m home. You hungry, kitty?”

“Who’s Frank?”

You whirl around, your heart pounding, and a low snicker comes from the shadowy corner beside the door.

_Pennywise._

But not _your_ Pennywise.

The clown-thing moves into the dim light, impossibly tall, slender limbs jutting from the cuffs of the pale-silk suit. He is lithe and long, with amber eyes and tufts of coppery hair. Smirking, showing those buck-teeth between red lips, he watches you closely, drinking in your fear as you struggle to regain your composure.

“Where’s Frank? What have you done to my cat?”

You finally manage to speak, your voice coming out in a frightened little squeak.

The clown shrugs, “Nobody here but us, sweetheart. And I don’t know about you, or your little pussy-cat, but I’m _starving_.”

His smile broadens into a grin, his teeth growing sharp, and you back away, reaching behind you for the table. You prop yourself up against it, your fingers biting hard into the smooth surface, and then you move quickly to the other side, using the table as a barrier between you and Pennywise. The clown advances, looking mildly annoyed, pouting like a bizarre child.

“Awww. No fair.” He waggles a finger at you, affecting a disapproving expression, “You don’t want to play with me, {y/n}? Only, you seemed to like it, last time. You seemed to like _me_.” His tone is jaunty and teasing at first, and then his face changes, his eyes darkening and his voice dropping, suddenly hostile, “Don’t you like me? Oh, I’ll be _sad_ if you don’t come and play with me…and I’m no fun at _all_ when I’m sad.”

Saliva drips from his fangs in long ropes, splattering to the floor.

_Well, that explains the mess in the hallway._

Your blood is thudding at your temples, almost painfully, and you swallow, forcing steel into your voice, “I don’t play with bullies.”

Pennywise flinches slightly, as though you have physically slapped him, and then he chuckles, leaning across the table and fixing you with those strange, wandering eyes, “It’s cute that you think you’ve got a choice here, angel-cake. I take _what_ I want, _when_ I want it, and right now I want to fuck you into oblivion. And you know what?” He presses a gloved finger against his lips, smirking deviously, “I think that’s what _you_ want, too. Don’t worry though, I won’t tell _Daddy_. It can be our little secret.”

For one terrifying moment, you’re certain that he’s about to leap over the table and take you, right here and now, on the kitchen floor, but then you hear the front door creak open and a voice calls out from the hallway.

“Hello? Hey, {y/n}?”

_It’s your best friend._

Pennywise glowers, rolling his eyes, “We’ll finish this later, sweet thing.” And then he disappears with a _pop_ , filling the air with the smell of popcorn and decay. Cursing under your breath, you open the kitchen window and the back door, in an attempt to dispel the lingering stench.

“You home, {y/n}? Hey loser, where are you?”

“Yeah, I’m in the kitchen, just gimme a minute…”

You quickly pull yourself together and move into the hallway, dimly aware that your legs are trembling. Your best friend is standing upon the doormat, stooping to gather up your mail and your discarded socks. They glance up, hearing your approach, “You making coffee?”

“Yeah, you want one?”

Your friend nods, “Sure, let me give you a hand.”

They step off the doormat, onto the wood flooring, and you recoil, suddenly remembering the clown’s mess. You move forward to grasp your friend’s elbow, ready to guide them around the drool trail, “Wait, watch out for the…”

For the _what_ , exactly?

You can’t say it.

Your friend raises an eyebrow, following your gaze, “What? What is it?”

_And then you remember that no one else can see the clowns._

_They can’t see the blood, or the carnage, or anything else that the clowns don’t want them to see._

_No one can, apart from the children._

_And you._

You force a smile, slackening your grip upon your friend’s arm, “It’s just… _the cat_ …Frank, he had a little accident.” You send a mental apology out to Frank, wherever he is, for laying the blame on him, “I cleaned it up, but I think I might have missed a bit. That’s why I took them off.” You gesture to your socks, which are hanging limply from your friend’s hand, “They’re wet.”

Your friend grimaces, immediately dropping the offending items of clothing, “Ugh! Oh man, that’s gross, {y/n}!”

You smile ruefully, heading for the kitchen, “You have no idea, believe me.”


	2. Chapter 2

As you had feared, the clown turns up at your house twice more within the space of a week. You manage to escape his advances by the skin of your teeth, albeit with saliva all over your floor and all over your _face_ , but he is seemingly relentless, and you don’t know how much longer you can get away with it.

And you have a horrible feeling that _your_ Penny is going to show up at some point, because you haven’t seen him a while, and he’ll walk in on you, with the _other_ Pennywise, and then he’ll…

Well, you really don’t know _what_ he’ll do, and you sure as shit don’t want to find out.

With this in mind, you take a day off work and head into the woods, hoping to catch Penny at the trailer. You’re not quite sure what you’re hoping to achieve; you want him to do something about the other clown, but you don’t want to escalate the situation. And besides, even though there’s a possibility that the new clown might be Penny’s kid, his _offspring_ , you seriously doubt that he’ll be able to exert any influence or power over him.

Anyway, that aside, you’re eager to see Penny. All this tension has got you pent up, _frustrated_ , and you need a good _fuck_ ; it’s been way too long since your last visit to the trailer.

You’re in luck, as it happens, because Penny is home and he’s more than ready to show you a wild time, judging by the way he shoves his tongue down your throat the moment you step inside.

“Missed me?”

You pull away, smirking, and he takes your jaw between strong fingers, devouring your face with hungry blue eyes. His other hand snakes down, between your thighs. _Oh, yes._ His fingers, ungloved, roughly grasping your cunt through your jeans. You moan, tilting your hips, and he smiles approvingly, “Missed _this_ , babydoll.”

You’re already so wet for him, so hot that you’re almost burning a hole in the crotch of your jeans. You whimper, grinding back and forth upon his hand, chasing that delicious friction, “Fuck me, Daddy.”

Penny clicks his tongue, moving his hand to the buttons of your blouses, “What’s the hurry, baby?” He opens your blouse at a leisurely pace, taking his sweet time about it, and you know that he’s _enjoying_ this, that he loves having you at his mercy, writhing miserably in his arms.

_One button at a time._

_Slowly._

_Oh, so slowly…_

And then your tits are out, soft and heavy in his warm palms, the nipples standing to attention in the cool air. He rubs his thumbs across them, until they’re so hard, almost _painfully_ hard, like little pink bullets.

“Gonna plough you, babydoll. Gonna take you nice and slow, nice and _deep_ , make sure you feel every inch of my cock inside your little pussy. You want it? Hmm?”

You nod frantically, arching your tits into his hands, “Oh yes, _yes_ I want it, please, oh _please_ …”

Penny chuckles, slinking away to the La-Z-Boy, “Show me, then. You want this?” He grabs at his crotch, running his tongue across his red lips; it’s so horrible, so _obscene_ , but your knees buckle at the sight and you _whine_ , like an animal in heat. The clown cackles at your wretchedness, “Show me, baby. Down on the floor, with your jeans down and your legs open wide. Show me how much you want my cock.”

Still whining piteously, you shuck your jeans over your hips and step out of them. Your panties follow, in a flurry of blue lace. You send them sailing across the room in your desperation to be rid of them, and they land in front of the La-Z-Boy, between Penny’s feet. He stoops to retrieve them, holds the gusset against his nose and _inhales_ noisily, sighing with exaggerated pleasure. He keeps his eyes on you the whole time.

You flush, dropping your gaze, and he laughs delightedly at your embarrassment, “Oh, you look so _pretty_ , {y/n}, with your cheeks all red and rosy. Like your sweet little ass, after a good spanking. My shy girl.”

You stand there awkwardly, like a virgin bride on her wedding night, clasping your arms across your breasts and the curve of your hips. Penny slips your panties into the pocket of his clown-suit, “Well? I’m waiting, baby. Don’t make me come over there.”

Still blushing, you stretch out on the floor, shivering at the coolness of the linoleum beneath your bare skin. Tentatively, you bend your knees and edge your feet apart, shifting your buttocks until you’re comfortable.

_As comfortable as you can manage at any rate, in such an undignified position._

Penny graces you with an approving smile, “Good. That’s real good, babydoll.”

You place your hands upon your thighs, trying to ignore the desperate quaking of your body, the tremors turning your muscles to jelly.

“Open your legs, doll.” Penny leans forward, his eyes bright with mischief as he urges you on, “Wider, _wider_ , come on…yeah, that’s it. Now spread your lips for me, spread that cunt open. Let me see it.”

You slip your fingers between your folds, holding yourself open, exposing the pink wetness of your slit. Your vulva feels puffy, swollen to the touch, and your hole is _drenched_ , your inner walls yielding immediately at the slightest touch.

Penny grunts appreciatively, “Get your fingers in there, princess. Go on.”

You close your eyes, wishing he’d give this up and just _fuck_ you, but there’s no use arguing; when Pennywise gets an idea in his head, that’s it.

_Tough shit._

Sighing, you sink your fingers into your cunt, hips juddering at the sensation. Within a few minutes, you’ve found a rhythm that suits you, and you’re sweating, wriggling on the floor. 

_Plunging your fingers in and out, again and again._

Climax evades you, and so you pinch your clit, and then you almost come undone, tits heaving with the effort. Penny encourages you, crooning in a low voice, through a fog of cigar-smoke, “Oh, you’re _good_ at this, baby. Must be all that practice, hmm? Oh yes, I’ve _seen_ you, when you think you’re alone. Lying in bed, fingering your little twat. Thinking of ol’ Pennywise…”

You gasp, thrusting wildly against your hand.

_So close…_

“Alright, that’s enough, doll.”

Penny is standing over you, sprinkling ash over your torso. He smirks, “Didn’t say you could cum yet, did I?”

You stop, mid-thrust, almost crying with frustration.

“I could watch you do that _all day long_ , baby. And maybe I will, one day. But first thing’s first…”

Penny takes his cock in hand; it’s hard and thick, smearing precum across his palm. He slides his fist over it, working his shaft with lazy strokes. You watch, your eyes hazy with desire, with _envy_ ; oh, you want to be his hand, you want to glide up and down his cock like that, but he’s content to leave you there, panting like a needy little bitch on the floor.

_He’s killing me, and he knows it._

_Smug bastard._

“You look so good lying there, {y/n}. Spread open for me. Might just have to cum right here and now, all over your face and your sweet tits.” His strokes quicken, his fingers tightening around his girth, “Won’t let you wash it off. You can walk home like that, covered in my cum. Let everyone in town see you for what you really are; Pennywise’s little clown-slut.”

_All this dirty talk is fucking torture._

_You actually want him to do it, to cum over you, but you want him inside you more._

“Pen, please…”

Suddenly, the trailer door _slams_ open, and you _scream_ , your hands flying up to cover as much of your naked skin as you can - which isn’t all that much, unfortunately. Penny whirls around, roaring obscenities, his eyes flashing red fire.

The other clown, the other Pennywise, is peering around the door, his lips stretched into a ludicrous grin. He chuckles, slinking inside.

“Room for one more?”


	3. Chapter 3

Penny shoves his cock out of sight, swearing loudly and glowering at the intruder. You scramble up onto the couch, tucking your legs beneath you, in a sad attempt at modesty.

_Absolutely ridiculous, really._

_Considering the last time the three of you were here, together in this trailer, the new guy had his tongue inside you, tasting your insides._

_And then he had fucked you raw, from behind, as you stretched your lips around Penny’s cock._

You uncoil your legs, feeling slightly foolish.

The tall clown pouts, folding his arms, “Aww, why’d you stop? You looked like you were having fun!”

Penny rolls his eyes, “Yeah, we _were_ , until you showed up.”

“Aww shucks.” The other Pennywise shuffles his huge feet, in mock abashment, “I just wanted to play with you guys. It’s kinda lonesome, down there in the sewers.”

“Well, deal with it, kid.” Penny stubs out his cigar, sinking moodily into the La-Z-Boy, “Go on, get outta here. Go find your own human.”

“C’mon, don’t be mean.” The second clown plonks himself down on the couch beside you, favouring you with a charmingly buck-toothed grin, “Remember, sharing is caring.”

You huff loudly, irritated by this disruption, “Oh geez, just let him stay, if he wants. I don’t care. I just…I _really_ need you now, Pen. Okay? _Please?_ ”

You’re still nervous around this clown, especially after his unwelcome visits to your house, but you’re beyond caring at this point; you just need to get _fucked_ , right now. All the teasing has pushed you to the edge. Hell, you can barely sit still, you’re so wound up; you’re shifting back and forth, rubbing your thighs together for scant relief, your breath coming in shallow pants.

Penny is still grumbling, eyeing the interloper with murderous intentions, but one look at your face is enough to sway him.

_And the look he gives you in return is enough to melt your loins._

_Affectionate and exasperated, long-suffering and all-consuming._

He clicks his fingers, his voice gruff, “Alright baby, on the floor.”

You’re down there before he can blink, spread open again, and he laughs at your eagerness, moving to kneel between your thighs. The other clown is perched upon the edge of the couch, his legs crossed. He looks like a child glued to their favourite Saturday cartoon, engrossed in the scene playing out before him.

“You gonna fuck her?”

Penny plants his hands upon your knees, pushing them apart. His eyes flicker upwards briefly, registering annoyance, but he does not deign to answer. He lowers his mouth to you, swiping his tongue across your clit in long, broad strokes. You groan, wrapping your legs over his shoulders, humping against his chin.

“Hey, are you gonna fuck her? Can I watch?”

Penny growls something, his voice muffled by your cunt. Whatever he said, you can’t make it out, but you suspect it’s something unpleasant. The other clown seems to understand, though. Telepathy does have its uses, after all. He lapses into silence, sulking on the couch, one eye drifting to the ceiling. The other eye is still fixed upon you, flickering over your body.

You’re too busy with Penny’s tongue to give a shit. He’s like a starving man at a feast, eating you, slurping noisily at your cunt, his face buried deep between your thighs. You suspect that he’s overegging it, trying to make the other clown jealous, but it feels so good that you give yourself up to it, reaching down to tangle your fingers into his red hair.

Eventually, the second Pennywise slides onto the floor, prowling around the pair of you like a tiger in a cage. After a few moments, he settles down beside you, trailing long fingers across your throat and your torso. His hand closes around one breast, squeezing lightly, and then _harder_ , rubbing his palm across your nipple. You let out a ragged sigh, arching into his touch, and Penny’s eyes snap up from between your slack legs, narrowing at the sight of the other clown, reclining on the floor with a handful of your tit.

The tall clown smirks cheekily and then he sticks his tongue out, the _absurdly long_ tongue that you already know so well, and allows to unfurl across your stomach, slapping wetly against your skin. He licks you, tasting your sweat, and then he curls the tip of his tongue around your nipple. You close your eyes, listening to your own hectic breathing.

_You can’t believe that you’re lying on the floor of a trailer, in the woods, your legs akimbo, with one alien clown eating you out and another running his hands and tongue all over your tits._

_Never in your wildest dreams, or nightmares, could you ever have imagined that this would happen to you._

Not that you’re complaining; you’ve already had three orgasms and you can feel yourself building up to a fourth. Suddenly, the second clown pulls away, moving to crouch beside Penny, who is still gorging himself upon your cunt.

“C’mon, lemme have a taste, it’s my turn…” His voice is high, affecting a whiny tone, “C’monnn, old man. Don’t be a greedy guts.” He paws at Penny’s shoulder, trying to prise him from between your thighs.

Penny finally comes up for air, his white face and red lips glistening with your juices, “Fuck off, you brat.”

You prop yourself up on your elbows, reaching out to trail your fingers across your clown’s snarling mouth, “Pen, let him have a turn. I want you up here, with me.” You sigh breathily, running your other hand over the tips of your breasts, back and forth, “I wanna suck your cock, Daddy. Please?”

Penny relents, grudgingly, and moves up to straddle your chest, grabbing a cushion from the couch along the way. The other clown plunges head-first into your cunt with a happy murmur, immediately suckling upon your engorged clit, like it’s a piece of hard candy. You yelp, compressing his face between your thighs.

“Here, baby.” Penny slides the cushion under your head, smirking down at you, “Don’t want you choking now, do we?”

You smile, taking his cock into your hand, “Only a little bit.”

Penny chuckles, “That’s my girl.” He rubs the head of his dick against your mouth, “Open up, princess.” You take him in, as far as you can in this awkward position, keeping one hand wrapped around his thick shaft, pumping lightly. He moves his hips slowly, his fingers twitching against your hair, “That’s it, babydoll. Suck my cock.”

You press your tongue against the underside of his length, feeling it pulsate. The second Pennywise is twisting his own tongue inside of you, making you cum over and over, and your moans vibrate around Penny’s cock, until he jolts deeper into your mouth, fucking your face. You can barely breathe, with your nose pressed flush against his groin, but you keep going, determined to prove yourself, to be the best little cock-sucker you can be; only the best, for your Daddy Pen.

Penny cums with a violent grunt, filling your mouth only seconds after another orgasm is racked from your quivering frame, making your toes curl against the other clown’s ears until your feet start to cramp. You make sure to swallow it all down, and he smiles proudly, patting your sweat-slicked hair, “You did so good, babydoll. So good.”

He moves back into the La-Z-Boy and lights a cigar, seemingly content to watch the second Pennywise have his fill of you. The tall clown is still between your thighs, slavering all over you, but you feel completely spent. You brush your fingers through his coppery hair, tugging lightly to pull him away from you. He growls, like a dog guarding a bone, but you manage to gently slide yourself from beneath him, smiling ruefully when he grabs at your ankles and tries to drag you back to him.

Penny smirks, blowing smoke into the air, “She’s only human, kid. Gotta let her rest, otherwise you’ll break her, you get me? And then I’ll be pissed.”

The tall clown huffs loudly, resting his chin in his hands, “So, I don’t get to cum tonight? How is that fair?”

Penny rolls his eyes, “You got a pair of hands, yeah? Use ‘em.”

“Fuck you, asshole.”

“Right back at ya, shitface.”

You wobble over to Penny, your legs threatening to give way at any moment, and press a kiss against his cheek, before collapsing onto the couch. Your eyes drift across to the second Pennywise, still sitting upon the floor, like a sullen child.

“Hey, come up here.” You murmur sleepily, reaching out to him, “I want to snuggle.”

He eyes you suspiciously, “I don’t…I don’t get it.” He glances at Penny, who is smoking and reading a book; _Dracula_ , by Bram Stoker.

The older clown shrugs, “You wanna cum? Yeah? Well then, I suggest you do as the lady says. She might be willing you help you out, once she’s had a nap.”

“And _this_ will help her nap? We don’t _snuggle_ , whatever the fuck that even is, but we still manage to sleep for twenty-seven years…”

Penny chuckles, “We’re not _human_ , you dick.”

The second Pennywise scowls, but the cogs are turning behind his amber eyes, pondering this new lesson. Finally, he climbs up onto the couch behind you, curling his long limbs around your limp frame. You wriggle against him, murmuring softly, and he slides his gaze across to Penny, who is watching with an expression of mingled amusement and jealousy. 

“See? Purring like a kitten.”

The tall clown snorts derisively, but his fingers creep into your hair. He isn’t as practised as Penny and his unsheathed claws snag upon your tangled curls. Still, it’s rather soothing.

_Ugh._

_Not for the first time, you question your sanity._

The younger clown is slowly coming around to the idea, but he isn’t completely sold yet. He looks at Penny again, unconvinced, “Do _you_ do this? With her?”

Penny leafs idly through the book upon his lap, drumming a finger against the length of his cigar, “Mmhmm. All the time.”

“Do you _like_ it?”

Penny allows his bright blue eyes to glide over your features. You can feel him looking at you, even through the mist of sheer exhaustion. You open your eyes, meeting his gaze without fear.

He smirks, turning his attentions back to _Dracula_ , the cigar burning out to ashes in his grip, “Yeah, it’s not bad.”

You smile, finally allowing sleep to claim you.


End file.
